2018
DOI: 10.1002/slct.201803007
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Aerobic Oxidation of Methyl‐substituted β‐Carbolines Catalyzed by N‐Hydroxyphthalimide and Metal Catalyst

Abstract: Carboxylic functionalized β‐carbolines were successfully synthesized in good to excellent yields and high selectivity under mild conditions by aerobic oxidation in the presence of NHPI and transition metal salt using molecular oxygen as an oxidizing agent. A variety of derivatives of fascaplysin thus are available for structure‐bioactivity investigations.

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Cited by 10 publications
(7 citation statements)
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“…Carbolines 1a , 1b , 1c , 1d , 1e , 1h and 1i were prepared according to the published procedures in the literature, and spectroscopic characterizations are in agreement with those reported . Compounds 1f , 1g , and 1j were prepared with acyl chloride and respective amines.…”
Section: Methodssupporting
confidence: 55%
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“…Carbolines 1a , 1b , 1c , 1d , 1e , 1h and 1i were prepared according to the published procedures in the literature, and spectroscopic characterizations are in agreement with those reported . Compounds 1f , 1g , and 1j were prepared with acyl chloride and respective amines.…”
Section: Methodssupporting
confidence: 55%
“…Synthesis schemes of compounds 1a – 1e , 1h , and 1i and 2a – 2e , 2h , and 2i are illustrated in Figure A, while synthesis of 1f , 1g , 1j , and 1k and 2f and 2g is described in Figure B. β-Carbolines and methyl-substituted derivatives 1 and corresponding fascaplysins 2 were prepared according to the published procedure. , Carboxylic β-carboline 1e underwent thermal-induced intramolecular nucleophilic substitution to yield 2e . Amide-modified β-carbolines were synthesized by condensation between acyl chloride prepared in situ and amine; the following cyclization reaction afforded amide-modified fascaplysin.…”
Section: Resultsmentioning
confidence: 99%
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“…Therefore, in this regard, due to the vulnerability of benzoyl group under harsh conditions, mild amidation protocol by coupling activated acid and amine is preferred to prepare β ‐carboline amides (Table ). β ‐Carboline‐6‐carboxylic acid 1 a and aniline 2 a , were used to optimize the reaction conditions of amidation. Direct thermal condensation between acid and amine failed to produce desired amide 3 a (entry 1).…”
Section: Resultsmentioning
confidence: 99%
“…Fascaplysin and 9-methylfascaplysin were synthesized via a two-step process from tryptamine and 5-methyltryptamine in 50–55% overall yields, according to published methods, as shown in Figure 1 [ 32 , 33 , 34 ]. The spectroscopic and spectrometric data of 3a matched with literature reports [ 35 ].…”
Section: Methodsmentioning
confidence: 99%